[NH2:1][C:2]1[C:3]([C:26](OCC)=[O:27])=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][OH:25])[CH:19]=2)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].OC1C=CC=CC=1[N:38](CC)N1C(C([O-])=O)=CC(NC2C=CC=CC=2OC)=NC1.[CH2:59]([OH:61])C>[Pd]>[OH:25][CH2:24][C:20]1[CH:19]=[C:18]([NH:17][C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:59](=[O:61])[N:8]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:3]([C:26]([NH2:38])=[O:27])[N:4]=2)[CH:23]=[CH:22][CH:21]=1Ethyl 5-amino-2-(3-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl-5-nitro-2-(3-(hydroxy(ethyl)phenylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate (0.35 g, 0.797 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.087 g) was added to the flask and flushed with fresh hydrogen gas and allowed to stir at room temperature. After 16 h, the reaction was filtered through celite and the filtrate condensed under reduced pressure. The crude oil was purified using biotage chromatography (50-100% ethyl acetate in hexanes) to afford the title compound (0.277 g, 85%). MS (ESI) m/z 410.5 [M+1]+.
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